EP1337262B1 - Solutions ophtalmiques et pour verres de contact ameliorees a source de peroxyde et conservateur cationique polymere - Google Patents

Solutions ophtalmiques et pour verres de contact ameliorees a source de peroxyde et conservateur cationique polymere Download PDF

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Publication number
EP1337262B1
EP1337262B1 EP01987313A EP01987313A EP1337262B1 EP 1337262 B1 EP1337262 B1 EP 1337262B1 EP 01987313 A EP01987313 A EP 01987313A EP 01987313 A EP01987313 A EP 01987313A EP 1337262 B1 EP1337262 B1 EP 1337262B1
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Prior art keywords
solutions
phmb
none
solution
peroxide
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German (de)
English (en)
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EP1337262A4 (fr
EP1337262A2 (fr
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Francis Xavier Smith
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FXS Ventures LLC
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FXS Ventures LLC
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/164—Amides, e.g. hydroxamic acids of a carboxylic acid with an aminoalcohol, e.g. ceramides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/327—Peroxy compounds, e.g. hydroperoxides, peroxides, peroxyacids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4172—Imidazole-alkanecarboxylic acids, e.g. histidine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00—Medicinal preparations containing inorganic active ingredients
    • A61K33/40—Peroxides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0048—Eye, e.g. artificial tears
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L12/00—Methods or apparatus for disinfecting or sterilising contact lenses; Accessories therefor
    • A61L12/08—Methods or apparatus for disinfecting or sterilising contact lenses; Accessories therefor using chemical substances
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L12/00—Methods or apparatus for disinfecting or sterilising contact lenses; Accessories therefor
    • A61L12/08—Methods or apparatus for disinfecting or sterilising contact lenses; Accessories therefor using chemical substances
    • A61L12/086—Container, accessories or devices therefor
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L12/00—Methods or apparatus for disinfecting or sterilising contact lenses; Accessories therefor
    • A61L12/08—Methods or apparatus for disinfecting or sterilising contact lenses; Accessories therefor using chemical substances
    • A61L12/12—Non-macromolecular oxygen-containing compounds, e.g. hydrogen peroxide or ozone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L12/00—Methods or apparatus for disinfecting or sterilising contact lenses; Accessories therefor
    • A61L12/08—Methods or apparatus for disinfecting or sterilising contact lenses; Accessories therefor using chemical substances
    • A61L12/12—Non-macromolecular oxygen-containing compounds, e.g. hydrogen peroxide or ozone
    • A61L12/124—Hydrogen peroxide; Peroxy compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L12/00—Methods or apparatus for disinfecting or sterilising contact lenses; Accessories therefor
    • A61L12/08—Methods or apparatus for disinfecting or sterilising contact lenses; Accessories therefor using chemical substances
    • A61L12/14—Organic compounds not covered by groups A61L12/10 or A61L12/12
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L12/00—Methods or apparatus for disinfecting or sterilising contact lenses; Accessories therefor
    • A61L12/08—Methods or apparatus for disinfecting or sterilising contact lenses; Accessories therefor using chemical substances
    • A61L12/14—Organic compounds not covered by groups A61L12/10 or A61L12/12
    • A61L12/141—Biguanides, e.g. chlorhexidine
    • A61L12/142—Polymeric biguanides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/04—Artificial tears; Irrigation solutions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
    • A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
    • A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame

Definitions

  • This invention relates to ophthalmic solutions used to treat eyes, to deliver active pharmaceutical agents to eyes and to treat ophthalmic devices that in use directly contact corneal tissues.
  • Ophthalmic solutions are used to regularly treat and condition eyes and articles and devices that are regularly used in eyes, such as contact lenses. Because of the intimate contact that such solutions have with corneal tissue, several problems or concerns are regularly presented. For instance, for solutions directly in contact with corneal tissue the compatibility of the solution with the tissue, its ability to not damage or irritate, is important. This compatibility issue is also important for solutions used to treat devices that contact corneal tissue, such as contact lenses and the like. Furthermore, prolonged contact with corneal tissue can lead to the accumulation of material on corneal tissue, or on devices in contact with the solution that then leads to adverse reactions.
  • Preservative efficacy is measured by the amount that a solution decreases the viability of bacterial or fungal populations.
  • preservative efficacy is measured by the amount that a solution decreases the viability of bacterial or fungal populations.
  • corneal tissue compatibility as well as “comfort.”
  • the field of the invention relates to preservative systems that are broad ranged, and effective against not only bacterial, but also fungal sources of infection.
  • US-A-5,449,658 discloses biocidal compositions comprising polyhexamethylene biguanide and EDTA, and methods for treating commercial and recreational water.
  • the growth of algae, fungi and pathogenic organisms in commercial and recreational waters, such as cooling towers, swimming pools and spas, may be controlled by adding to the water a primary sanitizing agent, preferably poly(hexamethylene biguanide) ("PHMB”), and a potentiating adjuvant comprising a calcium ion-chelating agent, preferably ethylenediamine tetraacetic acid (“EDTA”), in amounts such that the adjuvant renders the composition algicidal and fungicidal in water.
  • the water may be further treated with a peroxy salt as a backup agent, preferably sodium perborate, or the calcium ion-chelating agent and peroxy salt may be combined as a shock treatment to water being treated with the primary sanitizing agent.
  • WO-A-92/11876 discloses a method for disinfecting a contact lens comprising contacting the lens with an isotonic aqueous solution comprising 0.6 to 2 weight percent tromethamine (preferably 0.8 to 1.5 percent) for a time sufficient to disinfect the lens.
  • Other aspects include adding to the solution from 0.01 to 1 weight percent chelating agent (preferably disodium EDTA) and/or additional microbicide.
  • US-A-5,718,895 discloses enzymes with low isoelectric points for use in contact lens cleaning.
  • Compositions containing an ophthalmically acceptable, modified enzyme exhibiting a low pl and methods involving the combined use of these compositions with a polymeric antimicrobial agent, are disclosed for the simultaneous cleaning and disinfecting of contact lens.
  • the present invention relates to improved solutions used in ophthalmic applications, where the improvement is increased preservative and anti-microbial efficacy.
  • solutions comprising low levels of polyhexamethylene biguinide (PHMB) and a peroxide source, show increased preservative and anti-microbial activity over state of the art ophthalmic solutions.
  • PHMB polyhexamethylene biguinide
  • the present invention relates to ophthalmic solutions that are broad ranged and effective in low concentrations relative to state of the art systems.
  • ophthalmic solutions comprising 0.0100 to 0.0001 percent by weight of a peroxide producing agent and 0.1 to 500 parts per million by weight (PPM) of a cationic, polymeric preservative display an effective preservative capacity, and an increased capacity over state-of-the-art preservative systems.
  • PPM parts per million by weight
  • the invention also relates to articles of manufacture that employ the solution in their operation. For instance, vials employed to store contact lenses for sale may be filled using the solution.
  • the present invention relates to ophthalmic solutions that are broad ranged and effective in low concentrations relative to state of the art systems.
  • ophthalmic solutions comprising comprising 0.0100 to 0.0001 percent by weight of a peroxide producing agent and 0.1 to 500 parts per million by weight (PPM) of a cationic, polymeric display improved effective preservative capacity, and greater capacity over state-of-the-art preservative systems.
  • PPM parts per million by weight
  • Peroxide sources include hydrogen peroxide, sodium persulfate, sodium perborate decahydrate, sodium peroxide and urea peroxide.
  • peracetic acid an organic peroxy compound
  • the cationic polymeric preservative includes polymeric biguanides such as polymeric hexamethylene biguanides (PHMB), and combinations thereof.
  • polymeric biguanides such as polymeric hexamethylene biguanides (PHMB), and combinations thereof.
  • PHMB polymeric hexamethylene biguanides
  • water-soluble polymeric biguanides will have number average molecular weights of at least 1,000 and more preferably will have number average molecular weights from 1,000 to 50,000.
  • Suitable water-soluble salts of the free bases include, but are not limited to hydrochloride, borate, acetate, gluconate, sulfonate, tartrate and citrate salts.
  • polystyrene foams Most preferred are the polymeric hexamethylene biguanides, commercially available, for example, as the hydrochloride salt from Zeneca (Wilmington, Del.) under the trademark CosmocilTM CQ. Such polymers and water-soluble salts are referred to as polyhexamethylene (PHMB) or polyaminoptopyl biguanide (PAPB).
  • PHMB polyhexamethylene
  • PAPB polyaminoptopyl biguanide
  • polyhexamethylene biguanide is meant to encompass one or more biguanides have the following formula: wherein Z, X 1 and X 2 are as defined above and n is from 1 to 500.
  • the predominant compound falling within the above formula may have different X 1 and X 2 groups or the same groups, with lesser amounts of other compounds within the formula.
  • Such compounds are known and are disclosed in U.S. Pat. No. 4,758,595 and British Patent 1,432,345 .
  • the water-soluble salts are compounds where n has an average value of 2 to 15, most preferably 3 to 12.
  • a polymeric biguanide is used in combination with a bis(biguanide) compound.
  • Polymeric biguanides, in combination with bisbiguanides such as alexidine, are effective in concentrations as low as 0.00001 weight percent (0.1 ppm). It has also been found that the bactericidal activity of the solutions may be enhanced or the spectrum of activity broadened through the use of a combination of such polymeric biguanides with alexidine or similar biguanides.
  • An optional non-biguanide disinfectant/gennicide can be employed as a solution preservative, but it may also function to potentiate, complement or broaden the spectrum of microbiocidal activity of another germicide.
  • Suitable complementary germicidal agents include, but are not limited to, quaternary ammonium compounds or polymers, thimerosal or other phenylmercuric salts, sorbic acid, alkyl triethanolamines, and mixtures thereof.
  • quaternary ammonium compounds are compositions comprised of benzalkonium halides or, for example, balanced mixtures of n-alkyl dimethyl benzyl ammonium chlorides.
  • Other examples include polymeric quaternary ammonium salts used in ophthalmic applications such as poly[(dimethyliminio)-2-butene-1,4-diyl chloride], [4-tris(2-hydroxyethyl) ammonio]-2-butenyl-w-[tris(2-hydroxyethyl)ammonio]dichloride (chemical registry number 75345-27-6) generally available as polyquaternium 1 (r) from ONYX Corporation, or those described in U.S. Pat. No. 6,153,568 .
  • the acid-addition salts of the germicides used in the present composition may be derived from an inorganic or organic acid. In most circumstances it is preferable that the salts be derived from an acid which is readily water soluble and which affords an anion which is suitable for human usage, for example a pharmaceutically-acceptable anion.
  • acids are hydrochloric, hydrobromic, phosphoric, sulphuric, acetic, D-gluconic, 2-pyrrolidino-5-carboxylic, methanesulphonic, carbonic, lactic and glutamic acids.
  • Peroxide sources may also be included in the formulations of the present invention and are exemplified by hydrogen peroxide, and such compounds , which provide an effective resultant amount of hydrogen peroxide, such as sodium perborate decahydrate, sodium peroxide, urea peroxide and peracetic acid, an organic peroxy compound.
  • the pH of the present solutions should be maintained within the range of 5.0 to 8.0, more preferably about 6.0 to 8.0, most preferably about 6.5 to 7.8.
  • Suitable buffers may be added, such as boric acid, sodium borate, potassium citrate, citric acid, sodium bicarbonate, Bis-Tris Propane, TRIS, and various mixed phosphate buffers (including combinations of Na 2 HPO 4 , NaH 2 PO 4 and KH 2 PO 4 ) and mixtures thereof.
  • Borate buffers are useful for enhancing the efficacy of PAPB.
  • buffers will be used in amounts ranging from about 0.05 to 2.5 percent by weight, and preferably, from 0.1 to 1.5 percent.
  • solutions of the present invention may further contain other additives including buffers, tonicity agents, demulcents, wetting agents, preservatives, sequestering agents (chelating agents), surface active agents, and enzymes.
  • Ophthalmologically acceptable chelating agents useful in the present invention include amino carboxylic acid compounds or water-soluble salts thereof, including ethylenediaminetetraacetic acid, nitrilotriacetic acid, diethylenetriamine pentaacetic acid, hydroxyethylethylenediaminetriacetic acid, 1,2-diaminocyclohexanetetraacetic acid, ethylene glycol bis (beta-aminoethyl ether) in N, N, N', N' tetraacetic acid (EGTA), aminodiacetic acid and hydroxyethylamino diacetic acid.
  • These acids can be used in the form of their water soluble salts, particularly their alkali metal salts.
  • Especially preferred chelating agents are the di-, tn- and tetra-sodium salts of ethylenediaminetetraacetic acid (EDTA), most preferably disodium EDTA (Disodium Edetate).
  • citrates and polyphosphates can also be used in the present invention.
  • the citrates which can be used in the present invention include citric acid and its mono-, di-, and tri-alkaline metal salts.
  • the polyphosphates which can be used include pyrophosphates, triphosphates, tetraphosphates, trimetaphosphates, tetrametaphosphates, as well as more highly condensed phosphates in the form of the neutral or acidic alkali metal salts such as the sodium and potassium salts as well as the ammonium salt.
  • solutions of the invention are compatible with both rigid gas permeable and hydrophilic contact lenses and other ophthalmic devices and instruments during storage, cleaning, wetting, soaking, rinsing and disinfection.
  • a typical aqueous solution of the present invention may contain additional ingredients which would not affect the basic and novel characteristics of the active ingredients described earlier, such as tonicity agents, surfactants and viscosity inducing agents, which may aid in either the lens cleaning or in providing lubrication to the eye.
  • Suitable tonicity agents include sodium chloride, potassium chloride, glycerol or mixtures thereof
  • the tonicity of the solution is typically adjusted to approximately 240-310 milliosmoles per kilogram solution (mOsm/kg) to render the solution compatible with ocular tissue and with hydrophilic contact lenses.
  • the solution contains 0.01 to 0.5 weight percent sodium chloride.
  • the solutions employed in the present invention may also include surfactants such as a polyoxyethylene-polyoxypropylene nonionic surfactant which, for example, can be selected from the group of commercially available surfactants having the name poloxamine or poloxamer, as adopted by The CTFA International Cosmetic Ingredient Dictionary.
  • the poloxamine surfactants consist of a poly(oxypropylene)-poly(oxyethylene) adduct of ethylene diamine having a molecular weight from about 7,500 to about 27,000 wherein at least 40 weight percent of said adduct is poly(oxyethylene), has been found to be particularly advantageous for use in conditioning contact lenses when used in amounts from about 0.01 to about 15 weight percent.
  • Such surfactants are available from BASF Wyandotte Corp., Wyandotte, Mich., under the registered trademark "Tetronic”.
  • the poloxamers are an analogous series of surfactants and are polyoxyethylene, polyoxypropylene block polymers available from BASF Wyandotte Corp., Parsippany, N.J. 07054 under the trademark "Pluronic”.
  • the HLB of a surfactant is known to be a factor in determining the emulsification characteristics of a nonionic surfactant.
  • surfactants with lower HLB values are more lipophilic, while surfactants with higher HLB values are more hydrophilic.
  • the HLB values of various poloxamines and poloxamers are provided by BASF Wyandotte Corp., Wyandotte, Mich.
  • the HLB of the surfactant in the present invention is at least 18, more preferably 18 to 32, based on values reported by BASF.
  • surfactants that are known to be useful in contact wetting or rewetting solutions can be used in the solutions of this invention.
  • the surfactant should be soluble in the lens care solution and non-irritating to eye tissues.
  • Satisfactory non-ionic surfactants include polyethylene glycol esters of fatty acids, e.g. coconut, polysorbate, polyoxyethylene or polyoxypropylene ethers of higher alkanes (C 12 -C 18 ). Examples of the class include polysorbate 20 (available from ICI Americas Inc., Wilmington, Del.
  • Tween ® 20 polyoxyethylene (23) lauryl ether (Brij ® 35), polyoxyethylene (40) stearate (Myrj ® 52), polyoxyethylene (25) propylene glycol stearate (Atlas ® G 2612).
  • Brij ® 35, Myrj ® 52 and Atlas ® G 2612 are trademarks of, and are commercially available from, ICI Americas Inc., Wilmington, Del. 19897.
  • surfactants suitable for in the invention can be readily ascertained, in view of the foregoing description, from McCutcheon's Detergents and Emulsifiers, North American Edition, McCutcheon Division, MC Publishing Co., Glen Rock, N.J. 07452 and the CTFA International Cosmetic Ingredient Handbook, Published by The Cosmetic, Toiletry, and Fragrance Association, Washington, D.C . however, the preferred surfactants are commercially available surfactants sold under the trademark cremaphor tm by BASF and which are polyoxyethoxylated castor oils.
  • Suitable viscosity inducing agents can include lecithin or the cellulose derivatives such as hydroxymethylcellulose, hydroxypropylcellulose and methylcellulose in amounts similar to those for surfactants, above.
  • ** marketed product 2 having the general composition: A sterile, isotonic solution that contains HYDRANATE®(hydroxyalkylphosphonate), boric acid, edetate disodium, poloxamine, sodium borate and sodium chloride; preserved with DYMED® (polyaminopropyl biquanide) 0.0001%.
  • Formulations were prepared by dissolving L-histidine or Bis-Tris Propane in water. The pH of the solutions were adjusted to 7.3 with 1 N hydrochloric acid. Hydrogen peroxide, Dequest ® 2010 and polyhexamethylenebiguanide HCI (PHMB) were added to these solutions. The formulations were diluted to volume with water. Each of these solutions were tested for their activity against C. albicans (ATCC 10231) following a two hour exposure. The activity is expressed as a log reduction from the initial inoculum. The compositions, concentrations and activity of each of the solutions are summarized in the following table.
  • Formulations were prepared by dissolving L-histidine, Bis-Tris Propane, or Tricine in water. The pH of the solutions were adjusted to 7.3 with 1 N hydrochloric acid. Glycerin, hydrogen peroxide, Dequest 2010 and polyhexamethylenebiguanide HCl (PHMB) were added to these solutions. The formulations were diluted to volume with water. Each of these solutions were tested for their activity against C. albicans (ATCC 10231) following a two hour exposure. The activity is expressed as a log reduction from the initial inoculum. The compositions, concentrations and activity of each of the solutions are summarized in the following table.
  • Formulations were prepared by dissolving Tricine, Citiric Acid, Bicine, L-histidine,Glycine, or Lysine in water. The pH of the solutions were adjusted to 7.3 with 1 N hydrochloric acid. Hydrogen peroxide, Dequest ® 2010 and polyhexamethylenebiguanide HCl (PHMB) were added to these solutions. The formulations were diluted to volume with water. Each of these solutions were tested for their activity against C. albicans (ATCC 10231) following a two hour exposure. The activity is expressed as a log reduction from the initial inoculum. The compositions, concentrations and activity of each of the solutions are summarized in the following table.
  • Formulations were prepared by dissolving Bis-Tris Propane, L-histidine, or Tricine in water. The pH of the solutions were adjusted to 7.3 with 1 N hydrochloric acid. The tonicity agent, hydrogen peroxide, Dequest 2010 and polyhexamethylenebiguanide HCl (PHMB) were added to these solutions. The formulations were diluted to volume with water. Each of these solutions were tested for their activity against C. albicans (ATCC 10231) following a two hour exposure. The activity is expressed as a log reduction from the initial inoculum. The compositions, concentrations and activity of each of the solutions are summarized in the following table.

Claims (6)

  1. Solution ophtalmique comprenant de 0,01 à 0,0001 % en poids d'un agent de production de peroxyde choisi dans le groupe comprenant le peroxyde d'hydrogène, le peroxyde de sodium, le peroxyde d'urée et l'acide peracétique, et 0,1 à 500 parties par million d'un conservateur polymère cationique.
  2. Solution selon la revendication 1, dans laquelle le conservateur polymère cationique est représenté par la formule chimique :
    Figure imgb0008
     où Z est un groupe de pontage divalent organique qui peut être le même dans tout le polymère ou être différent, n est en moyenne au moins égal à 3, et X1 et X2 sont choisis dans le groupe comprenant :
    Figure imgb0009
  3. Solution selon la revendication 2, dans laquelle n est en moyenne compris entre 5 et 20.
  4. Solution selon la revendication 1, comprenant en outre de 0,05 à 2,5 % en poids d'une solution tampon choisie dans le groupe comprenant l'acide borique, le borate de sodium, le citrate de potassium, l'acide citrique, le bicarbonate de sodium, le TRIS, le Na2HPO4, le NaH2PO4, et le KH2PO4, et leurs mélanges.
  5. Solution selon la revendication 4, comprenant en outre un agent de surface.
  6. Fiole pour lentille de contact comprenant :
    une fiole ;
    une lentille de contact ; et
    une solution en quantité suffisante pour immerger la lentille de contact, la solution comprenant entre 0,01 et 0,0001 % en poids d'un agent de production de peroxyde et entre 0,1 et 500 ppm d'un conservateur polymère cationique.
EP01987313A 2000-11-08 2001-11-08 Solutions ophtalmiques et pour verres de contact ameliorees a source de peroxyde et conservateur cationique polymere Expired - Lifetime EP1337262B1 (fr)

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EP01993437A Expired - Lifetime EP1339414B1 (fr) 2000-11-08 2001-11-08 L-histidine dans des solutions ophtalmiques
EP01987313A Expired - Lifetime EP1337262B1 (fr) 2000-11-08 2001-11-08 Solutions ophtalmiques et pour verres de contact ameliorees a source de peroxyde et conservateur cationique polymere
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WO2002040062A2 (fr) 2002-05-23
CN1263463C (zh) 2006-07-12
JP2004512901A (ja) 2004-04-30
WO2002040062A3 (fr) 2002-09-06
WO2002038077A3 (fr) 2002-07-25
EP1992340A1 (fr) 2008-11-19
JP5301498B2 (ja) 2013-09-25
ATE405265T1 (de) 2008-09-15
AU2002225950B2 (en) 2006-08-10
ES2311035T3 (es) 2009-02-01
DK1337262T3 (da) 2008-12-15
EP1331902A2 (fr) 2003-08-06
WO2002062260A3 (fr) 2002-10-17
EP1339414A2 (fr) 2003-09-03
CN1212848C (zh) 2005-08-03
PT1337262E (pt) 2008-10-24
JP2013122609A (ja) 2013-06-20
JP5868338B2 (ja) 2016-02-24
CN1212847C (zh) 2005-08-03
ES2337446T3 (es) 2010-04-26
EP1339414A4 (fr) 2006-03-15
DE60135478D1 (de) 2008-10-02
PT1331902E (pt) 2008-12-02
WO2002038077A2 (fr) 2002-05-16
CN1505520A (zh) 2004-06-16
JP4580143B2 (ja) 2010-11-10
DK1339414T3 (da) 2010-04-19
CA2428997A1 (fr) 2002-05-23
ES2578679T3 (es) 2016-07-29
ATE406167T1 (de) 2008-09-15
DE60141039D1 (de) 2010-02-25
CN1486186A (zh) 2004-03-31
CA2434961C (fr) 2010-05-25
EP1337262A4 (fr) 2006-02-08
JP2016040613A (ja) 2016-03-24
EP1331902B1 (fr) 2008-08-20
PT1339414E (pt) 2010-03-03
AU2595002A (en) 2002-05-21
DE60135572D1 (de) 2008-10-09
CY1110596T1 (el) 2015-04-29
DK1331902T3 (da) 2008-12-08
US20060078626A1 (en) 2006-04-13
CY1108439T1 (el) 2014-04-09
CY1108438T1 (el) 2014-04-09
JP2004526186A (ja) 2004-08-26
AU3954502A (en) 2002-05-27
CN1486187A (zh) 2004-03-31
EP3045168A1 (fr) 2016-07-20
JP5923211B2 (ja) 2016-05-24
JP2010266867A (ja) 2010-11-25
JP2004525865A (ja) 2004-08-26
EP1331902A4 (fr) 2006-02-08
EP1339414B1 (fr) 2010-01-06
EP1337262A2 (fr) 2003-08-27
WO2002062260A2 (fr) 2002-08-15
AU2002251685B8 (en) 2006-06-15
AU2002251685B2 (en) 2005-10-27
CA2428994C (fr) 2010-05-11
ATE454157T1 (de) 2010-01-15
AU2002239545B2 (en) 2006-10-05
CA2428994A1 (fr) 2002-08-15
ES2311555T3 (es) 2009-02-16
JP5258139B2 (ja) 2013-08-07
EP1992340B1 (fr) 2016-05-11
CA2434961A1 (fr) 2002-05-16

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